Tons of rules here which make a condo association "warrantable" vs "non-warrantable" but just one on the list: one owner owning the majority of the units alone will typically make them non-warrantable.

The webpage has them based in Maryland but they aren't listed in the state's business directory.

We were upset when they listed it without letting us know...

Then once you've fixed the property up and at least have it listed for rent you could refinance into a DSCR loan.

However it is not listed in the top 10 of highest demand cities (most bookings) or most listings.

Ended up picking up the property for $162,500 from a listing price of $175,000.

Used the listing agent to represent us both.

You could make this work ST, MT or LT, depending on how you approach it - the key with unique grounds is owner-provided upkeep and service built into the listing and what permits allow. 

Obviously the answer is yes when it comes down to the cash flow, but I am particularly wondering if HCOL/high property tax areas are places you would cross off the list entirely.

Make sure pool is listed on your insurance policy.